CA1086727A - Benzimidazole derivatives - Google Patents
Benzimidazole derivativesInfo
- Publication number
- CA1086727A CA1086727A CA291,976A CA291976A CA1086727A CA 1086727 A CA1086727 A CA 1086727A CA 291976 A CA291976 A CA 291976A CA 1086727 A CA1086727 A CA 1086727A
- Authority
- CA
- Canada
- Prior art keywords
- hydrogen
- radical
- formula
- remainder
- radicals
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title description 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- 238000000034 method Methods 0.000 claims abstract description 36
- 230000008569 process Effects 0.000 claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- -1 C1-6-alkyl radicals Chemical class 0.000 claims description 57
- 239000001257 hydrogen Substances 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 55
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 48
- 239000000460 chlorine Substances 0.000 claims description 37
- 239000007858 starting material Substances 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 10
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical compound C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 claims description 3
- RJIXIIOSXWJCPX-UHFFFAOYSA-N 8-benzoyl-4-methyl-4,10-dihydro-3h-pyrimido[1,2-a]benzimidazol-2-one Chemical compound C=1C=C2N3C(C)CC(=O)NC3=NC2=CC=1C(=O)C1=CC=CC=C1 RJIXIIOSXWJCPX-UHFFFAOYSA-N 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 1
- FFZKHULPLWYDQD-UHFFFAOYSA-N 12,14-dioxa-2,6,8-triazatetracyclo[7.7.0.02,7.011,15]hexadeca-1(16),7,9,11(15)-tetraen-5-one Chemical compound C1=C2N3CCC(=O)NC3=NC2=CC2=C1OCO2 FFZKHULPLWYDQD-UHFFFAOYSA-N 0.000 claims 1
- SPVQXWWWBMKQGE-UHFFFAOYSA-N 4,10-dihydro-3h-pyrimido[1,2-a]benzimidazol-2-one Chemical compound C1=CC=C2N3CCC(=O)NC3=NC2=C1 SPVQXWWWBMKQGE-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 210000001772 blood platelet Anatomy 0.000 abstract description 15
- 238000004220 aggregation Methods 0.000 abstract description 8
- 230000002776 aggregation Effects 0.000 abstract description 8
- 238000001727 in vivo Methods 0.000 abstract description 6
- 238000011282 treatment Methods 0.000 abstract description 4
- 208000007536 Thrombosis Diseases 0.000 abstract description 3
- 238000000338 in vitro Methods 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- 238000011321 prophylaxis Methods 0.000 abstract description 3
- 208000019553 vascular disease Diseases 0.000 abstract description 3
- GJYVNFASHFTWEU-UHFFFAOYSA-N 8-acetyl-4,10-dihydro-3h-pyrimido[1,2-a]benzimidazol-2-one Chemical compound C1CC(=O)NC2=NC3=CC(C(=O)C)=CC=C3N21 GJYVNFASHFTWEU-UHFFFAOYSA-N 0.000 abstract description 2
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 70
- 239000000203 mixture Substances 0.000 description 61
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- 239000000243 solution Substances 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 239000007787 solid Substances 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- 239000013078 crystal Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 238000004452 microanalysis Methods 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 5
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 206010043554 thrombocytopenia Diseases 0.000 description 5
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 4
- 102000008186 Collagen Human genes 0.000 description 4
- 108010035532 Collagen Proteins 0.000 description 4
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 4
- 229920001436 collagen Polymers 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- IFODSVOKJRKVAH-UHFFFAOYSA-N 5,6-di(propan-2-yloxy)-1h-benzimidazol-2-amine Chemical compound C1=C(OC(C)C)C(OC(C)C)=CC2=C1NC(N)=N2 IFODSVOKJRKVAH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 101100097467 Arabidopsis thaliana SYD gene Proteins 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 101100495925 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr3 gene Proteins 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 230000010354 integration Effects 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- URLKBWYHVLBVBO-UHFFFAOYSA-N p-dimethylbenzene Natural products CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 3
- ASVPUUDJBLBNEH-UHFFFAOYSA-N 1-(2-amino-3h-benzimidazol-5-yl)ethanone Chemical compound CC(=O)C1=CC=C2N=C(N)NC2=C1 ASVPUUDJBLBNEH-UHFFFAOYSA-N 0.000 description 2
- GPMHHSJZGVOEFS-UHFFFAOYSA-N 2-Amino-5-benzoylbenzimidazole Chemical compound C1=C2NC(N)=NC2=CC=C1C(=O)C1=CC=CC=C1 GPMHHSJZGVOEFS-UHFFFAOYSA-N 0.000 description 2
- PNMKRBOIMTZVLQ-UHFFFAOYSA-N 2-amino-3h-benzimidazole-5-carbonitrile Chemical compound C1=C(C#N)C=C2NC(N)=NC2=C1 PNMKRBOIMTZVLQ-UHFFFAOYSA-N 0.000 description 2
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical class NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 2
- RRJIGHUKYPLKIW-UHFFFAOYSA-N 5-chloro-6-methyl-1h-benzimidazol-2-amine Chemical compound C1=C(Cl)C(C)=CC2=C1NC(N)=N2 RRJIGHUKYPLKIW-UHFFFAOYSA-N 0.000 description 2
- WPMJALPQMIIHOE-UHFFFAOYSA-N 5-ethylsulfanyl-2-nitroaniline Chemical compound CCSC1=CC=C([N+]([O-])=O)C(N)=C1 WPMJALPQMIIHOE-UHFFFAOYSA-N 0.000 description 2
- FCEFZMUBBPBDBN-UHFFFAOYSA-N 6-ethylsulfanyl-1h-benzimidazol-2-amine Chemical compound CCSC1=CC=C2N=C(N)NC2=C1 FCEFZMUBBPBDBN-UHFFFAOYSA-N 0.000 description 2
- RHIPJPVWXDTEOX-UHFFFAOYSA-N 6-methylsulfanyl-1h-benzimidazol-2-amine Chemical compound CSC1=CC=C2N=C(N)NC2=C1 RHIPJPVWXDTEOX-UHFFFAOYSA-N 0.000 description 2
- MELMCGUWWNPXAX-UHFFFAOYSA-N 7-chloro-8-methyl-4,10-dihydro-3h-pyrimido[1,2-a]benzimidazol-2-one Chemical compound N1=C2NC(=O)CCN2C2=C1C=C(C)C(Cl)=C2 MELMCGUWWNPXAX-UHFFFAOYSA-N 0.000 description 2
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- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
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- WYRSGXAIHNMKOL-UHFFFAOYSA-N $l^{1}-sulfanylethane Chemical compound CC[S] WYRSGXAIHNMKOL-UHFFFAOYSA-N 0.000 description 1
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- YBDBYPQFIMSFJW-UHFFFAOYSA-N (4-chloro-3-nitrophenyl)-phenylmethanone Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(C(=O)C=2C=CC=CC=2)=C1 YBDBYPQFIMSFJW-UHFFFAOYSA-N 0.000 description 1
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- WZXFIDXRXIOGTR-UHFFFAOYSA-N 1,3-benzodioxole-4,5-diamine Chemical compound NC1=CC=C2OCOC2=C1N WZXFIDXRXIOGTR-UHFFFAOYSA-N 0.000 description 1
- ZCFSWYZFGJAUKK-UHFFFAOYSA-N 1,4-dimethyl-2,3-dinitrobenzene Chemical class CC1=CC=C(C)C([N+]([O-])=O)=C1[N+]([O-])=O ZCFSWYZFGJAUKK-UHFFFAOYSA-N 0.000 description 1
- YHDWKSALBRHRCQ-UHFFFAOYSA-N 1-(2-amino-3h-benzimidazol-5-yl)butan-1-one Chemical compound CCCC(=O)C1=CC=C2N=C(N)NC2=C1 YHDWKSALBRHRCQ-UHFFFAOYSA-N 0.000 description 1
- VEIXVSPCPGWULB-UHFFFAOYSA-N 1-(4-amino-3-nitrophenyl)ethanone Chemical compound CC(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 VEIXVSPCPGWULB-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- PHPYXVIHDRDPDI-UHFFFAOYSA-N 2-bromo-1h-benzimidazole Chemical compound C1=CC=C2NC(Br)=NC2=C1 PHPYXVIHDRDPDI-UHFFFAOYSA-N 0.000 description 1
- AYPSHJCKSDNETA-UHFFFAOYSA-N 2-chloro-1h-benzimidazole Chemical compound C1=CC=C2NC(Cl)=NC2=C1 AYPSHJCKSDNETA-UHFFFAOYSA-N 0.000 description 1
- KIZQNNOULOCVDM-UHFFFAOYSA-N 2-hydroxyethyl(trimethyl)azanium;hydrate Chemical compound O.C[N+](C)(C)CCO KIZQNNOULOCVDM-UHFFFAOYSA-N 0.000 description 1
- JCRWHUMNIOSWNT-UHFFFAOYSA-N 2-oxo-4,10-dihydro-3h-pyrimido[1,2-a]benzimidazole-8-carbonitrile Chemical compound N#CC1=CC=C2N3CCC(=O)NC3=NC2=C1 JCRWHUMNIOSWNT-UHFFFAOYSA-N 0.000 description 1
- VWLLPPSBBHDXHK-UHFFFAOYSA-N 3,4-diaminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1N VWLLPPSBBHDXHK-UHFFFAOYSA-N 0.000 description 1
- RZBWGEXTRWUGBV-UHFFFAOYSA-N 3,6-dimethylbenzene-1,2-diamine Chemical compound CC1=CC=C(C)C(N)=C1N RZBWGEXTRWUGBV-UHFFFAOYSA-N 0.000 description 1
- AXJLWOZOUQAJCH-UHFFFAOYSA-N 3-(2-amino-5-cyanobenzimidazol-1-yl)propanoic acid Chemical compound N#CC1=CC=C2N(CCC(O)=O)C(N)=NC2=C1 AXJLWOZOUQAJCH-UHFFFAOYSA-N 0.000 description 1
- ZUHBTVJKGTWMGK-UHFFFAOYSA-N 3-(2-aminobenzimidazol-1-yl)propanenitrile Chemical compound C1=CC=C2N(CCC#N)C(N)=NC2=C1 ZUHBTVJKGTWMGK-UHFFFAOYSA-N 0.000 description 1
- AFSDRVUYYAKKAE-UHFFFAOYSA-N 3-(4-benzoyl-2-nitroanilino)propanoic acid Chemical compound C1=C([N+]([O-])=O)C(NCCC(=O)O)=CC=C1C(=O)C1=CC=CC=C1 AFSDRVUYYAKKAE-UHFFFAOYSA-N 0.000 description 1
- HOYFZPFXOIOCNQ-UHFFFAOYSA-N 3-(4-cyano-2-nitroanilino)propanoic acid Chemical compound OC(=O)CCNC1=CC=C(C#N)C=C1[N+]([O-])=O HOYFZPFXOIOCNQ-UHFFFAOYSA-N 0.000 description 1
- YJHHPOVQQUWTCH-UHFFFAOYSA-N 3-(5-acetyl-2-aminobenzimidazol-1-yl)propanoic acid Chemical compound CC(=O)C1=CC=C2N(CCC(O)=O)C(N)=NC2=C1 YJHHPOVQQUWTCH-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- MAODRSNVSCQCBQ-UHFFFAOYSA-N 3-methylsulfanylbenzene-1,2-diamine Chemical compound CSC1=CC=CC(N)=C1N MAODRSNVSCQCBQ-UHFFFAOYSA-N 0.000 description 1
- ZSAWWJYNDFERFN-UHFFFAOYSA-N 4,7-dimethyl-1h-benzimidazol-2-amine Chemical compound CC1=CC=C(C)C2=C1N=C(N)N2 ZSAWWJYNDFERFN-UHFFFAOYSA-N 0.000 description 1
- HOFKXNBVTNUDSH-UHFFFAOYSA-N 4-chloro-5-methylbenzene-1,2-diamine Chemical compound CC1=CC(N)=C(N)C=C1Cl HOFKXNBVTNUDSH-UHFFFAOYSA-N 0.000 description 1
- POWPTEBMSHLSRA-UHFFFAOYSA-N 5,6-dimethoxy-1h-benzimidazol-2-amine Chemical compound C1=C(OC)C(OC)=CC2=C1NC(N)=N2 POWPTEBMSHLSRA-UHFFFAOYSA-N 0.000 description 1
- YPFQISHSXCFZMU-UHFFFAOYSA-N 5,6-dimethyl-1h-benzimidazol-2-amine Chemical compound C1=C(C)C(C)=CC2=C1NC(N)=N2 YPFQISHSXCFZMU-UHFFFAOYSA-N 0.000 description 1
- OPGUZRRLMQSMAQ-UHFFFAOYSA-N 5-(4-methoxyphenyl)-1-phenylbenzimidazole Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N(C=N2)C=3C=CC=CC=3)C2=C1 OPGUZRRLMQSMAQ-UHFFFAOYSA-N 0.000 description 1
- AKDHQKIGPDFQSP-UHFFFAOYSA-N 6,8-dimethyl-4,10-dihydro-3h-pyrimido[1,2-a]benzimidazol-2-one Chemical compound C1CC(=O)NC2=NC3=CC(C)=CC(C)=C3N21 AKDHQKIGPDFQSP-UHFFFAOYSA-N 0.000 description 1
- ANZGAGYAWCRIOP-UHFFFAOYSA-N 7,8-dimethyl-4,10-dihydro-3h-pyrimido[1,2-a]benzimidazol-2-one Chemical compound N1=C2NC(=O)CCN2C2=C1C=C(C)C(C)=C2 ANZGAGYAWCRIOP-UHFFFAOYSA-N 0.000 description 1
- DQOQDGKAPKGFGY-UHFFFAOYSA-N 8-ethylsulfanyl-4,10-dihydro-3h-pyrimido[1,2-a]benzimidazol-2-one Chemical compound C1CC(=O)NC2=NC3=CC(SCC)=CC=C3N21 DQOQDGKAPKGFGY-UHFFFAOYSA-N 0.000 description 1
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000005528 B01AC05 - Ticlopidine Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010010356 Congenital anomaly Diseases 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- UOACKFBJUYNSLK-XRKIENNPSA-N Estradiol Cypionate Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H](C4=CC=C(O)C=C4CC3)CC[C@@]21C)C(=O)CCC1CCCC1 UOACKFBJUYNSLK-XRKIENNPSA-N 0.000 description 1
- ZFDIRQKJPRINOQ-HWKANZROSA-N Ethyl crotonate Chemical compound CCOC(=O)\C=C\C ZFDIRQKJPRINOQ-HWKANZROSA-N 0.000 description 1
- MUQNGPZZQDCDFT-JNQJZLCISA-N Halcinonide Chemical group C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@@H]2O MUQNGPZZQDCDFT-JNQJZLCISA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241000786363 Rhampholeon spectrum Species 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 1
- 238000006480 benzoylation reaction Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- PCDHSSHKDZYLLI-UHFFFAOYSA-N butan-1-one Chemical compound CCC[C]=O PCDHSSHKDZYLLI-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 1
- 229960001214 clofibrate Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 1
- 229960002768 dipyridamole Drugs 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 239000002032 methanolic fraction Substances 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- NDRUTHFTDCUQOA-UHFFFAOYSA-N methyl 2-[4-(2-aminoacetyl)phenoxy]acetate Chemical compound COC(=O)COC1=CC=C(C(=O)CN)C=C1 NDRUTHFTDCUQOA-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 210000004623 platelet-rich plasma Anatomy 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- MBGGBVCUIVRRBF-UHFFFAOYSA-N sulfinpyrazone Chemical compound O=C1N(C=2C=CC=CC=2)N(C=2C=CC=CC=2)C(=O)C1CCS(=O)C1=CC=CC=C1 MBGGBVCUIVRRBF-UHFFFAOYSA-N 0.000 description 1
- 229960003329 sulfinpyrazone Drugs 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 description 1
- 229960005001 ticlopidine Drugs 0.000 description 1
- ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Hematology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB51426/76 | 1976-12-09 | ||
| GB51426/76A GB1585965A (en) | 1976-12-09 | 1976-12-09 | 3,4-dihydropyrimido (1,2 - )benzimidazol - 2(1h) - ones |
| GB33341/77 | 1977-08-09 | ||
| GB3334177 | 1977-08-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1086727A true CA1086727A (en) | 1980-09-30 |
Family
ID=26261828
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA291,976A Expired CA1086727A (en) | 1976-12-09 | 1977-11-29 | Benzimidazole derivatives |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4167569A (cs) |
| JP (1) | JPS5390296A (cs) |
| AT (1) | AT359068B (cs) |
| AU (1) | AU514427B2 (cs) |
| CA (1) | CA1086727A (cs) |
| CH (1) | CH633291A5 (cs) |
| CS (1) | CS199696B2 (cs) |
| DD (1) | DD133330A5 (cs) |
| DE (1) | DE2754930A1 (cs) |
| ES (1) | ES464862A1 (cs) |
| FI (1) | FI63577C (cs) |
| FR (1) | FR2373543A1 (cs) |
| GR (1) | GR65298B (cs) |
| HU (1) | HU176540B (cs) |
| IE (1) | IE45924B1 (cs) |
| IL (1) | IL53507A (cs) |
| IT (1) | IT1143729B (cs) |
| NL (1) | NL7713658A (cs) |
| NO (1) | NO774216L (cs) |
| NZ (1) | NZ185823A (cs) |
| PL (1) | PL107142B1 (cs) |
| SE (1) | SE435385B (cs) |
| SU (1) | SU843751A3 (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE51802B1 (en) * | 1979-12-03 | 1987-04-01 | Fujisawa Pharmaceutical Co | Quinazoline derivatives,processes for their preparation and pharmaceutical compositions containing them |
| CA1157858A (en) | 1979-12-03 | 1983-11-29 | Ikuo Ueda | Quinazoline derivatives |
| DE3208218A1 (de) * | 1982-03-06 | 1983-09-08 | Basf Ag, 6700 Ludwigshafen | Isoindolinfarbstoffe und deren verwendung |
| RU2394824C1 (ru) * | 2008-12-25 | 2010-07-20 | Государственное научное учреждение Северо-Кавказский зональный научно-исследовательский ветеринарный институт Российской академии сельскохозяйственных наук | ПРОИЗВОДНЫЕ ПИРИДО [1,2-a]БЕНЗИМИДАЗОЛА, ОБЛАДАЮЩИЕ АНТИБАКТЕРИАЛЬНЫМ ДЕЙСТВИЕМ, И СПОСОБ ИХ ПОЛУЧЕНИЯ |
| MY167785A (en) | 2012-06-27 | 2018-09-25 | 4Sg Ag | Bifluorodioxalane-amino-benzimidazole kinase inhibitors for the treatment of cancer, autoimmuneinflammation and cns disorders |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3468888A (en) * | 1967-04-11 | 1969-09-23 | Smithkline Corp | 2-substituted pyrimido(1,2-a) benzimidazoles |
| US3988340A (en) * | 1975-01-23 | 1976-10-26 | Bristol-Myers Company | 6-Alkoxymethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-ones and 7-alkoxymethyl-6-[H]-1,2,3,4-tetrahydropyrimido[2,1-b]quinazolin-2-ones |
| US4072679A (en) * | 1976-06-15 | 1978-02-07 | E. R. Squibb & Sons, Inc. | 1,4- AND 4,10-DIHYDRO-4-OXO-PYRIMIDO (1,2-A)-benzimidazole-3-carboxylic acids, esters and amides |
-
1977
- 1977-11-23 US US05/855,003 patent/US4167569A/en not_active Expired - Lifetime
- 1977-11-28 IE IE2408/77A patent/IE45924B1/en unknown
- 1977-11-29 CA CA291,976A patent/CA1086727A/en not_active Expired
- 1977-11-30 NZ NZ185823A patent/NZ185823A/xx unknown
- 1977-12-01 IL IL53507A patent/IL53507A/xx unknown
- 1977-12-01 AU AU31121/77A patent/AU514427B2/en not_active Expired
- 1977-12-05 HU HU77IE816A patent/HU176540B/hu unknown
- 1977-12-07 DD DD7700202450A patent/DD133330A5/xx unknown
- 1977-12-07 GR GR54931A patent/GR65298B/el unknown
- 1977-12-07 ES ES464862A patent/ES464862A1/es not_active Expired
- 1977-12-08 NO NO774216A patent/NO774216L/no unknown
- 1977-12-08 SE SE7713958A patent/SE435385B/sv unknown
- 1977-12-08 CH CH1507777A patent/CH633291A5/de not_active IP Right Cessation
- 1977-12-08 PL PL1977202753A patent/PL107142B1/pl unknown
- 1977-12-08 FR FR7737011A patent/FR2373543A1/fr active Granted
- 1977-12-09 NL NL7713658A patent/NL7713658A/xx not_active Application Discontinuation
- 1977-12-09 SU SU772552626A patent/SU843751A3/ru active
- 1977-12-09 AT AT883677A patent/AT359068B/de not_active IP Right Cessation
- 1977-12-09 DE DE19772754930 patent/DE2754930A1/de not_active Withdrawn
- 1977-12-09 IT IT30558/77A patent/IT1143729B/it active
- 1977-12-09 CS CS778270A patent/CS199696B2/cs unknown
- 1977-12-09 JP JP14866977A patent/JPS5390296A/ja active Pending
- 1977-12-09 FI FI773724A patent/FI63577C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2373543B1 (cs) | 1980-05-16 |
| JPS5390296A (en) | 1978-08-08 |
| SU843751A3 (ru) | 1981-06-30 |
| DD133330A5 (de) | 1978-12-27 |
| GR65298B (en) | 1980-08-01 |
| ATA883677A (de) | 1980-03-15 |
| CS199696B2 (en) | 1980-07-31 |
| IL53507A0 (en) | 1978-03-10 |
| PL202753A1 (pl) | 1978-10-09 |
| US4167569A (en) | 1979-09-11 |
| NL7713658A (nl) | 1978-06-13 |
| AU514427B2 (en) | 1981-02-12 |
| AT359068B (de) | 1980-10-27 |
| AU3112177A (en) | 1979-06-07 |
| NZ185823A (en) | 1980-08-26 |
| DE2754930A1 (de) | 1978-06-15 |
| PL107142B1 (pl) | 1980-01-31 |
| IE45924L (en) | 1978-06-09 |
| SE435385B (sv) | 1984-09-24 |
| HU176540B (en) | 1981-03-28 |
| IT1143729B (it) | 1986-10-22 |
| FR2373543A1 (fr) | 1978-07-07 |
| FI63577C (fi) | 1983-07-11 |
| FI63577B (fi) | 1983-03-31 |
| IE45924B1 (en) | 1982-12-29 |
| SE7713958L (sv) | 1978-06-10 |
| IL53507A (en) | 1981-07-31 |
| CH633291A5 (de) | 1982-11-30 |
| ES464862A1 (es) | 1979-01-01 |
| NO774216L (no) | 1978-06-12 |
| FI773724A7 (fi) | 1978-06-10 |
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| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |